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Summary: Triterpene skeletons, catalyzing by 2,3‐oxidosqualene cyclases (OSCs), are essential for synthesis of steroids and triterpenoids. In japonica rice cultivars Zhonghua11, a total of 12 OsOSCs have been found. While the catalytic functions of OsOSC1, 3, 4, 9, and 10 remain unclear, the functions of the other OsOSCs have been well studied.In this study, we conducted a comprehensive analysis of 12 OSC genes within genus Oryza with the aid of 63 genomes from cultivated and wild rice. We found that OSC genes are relatively conserved within genus Oryza with a few exceptions. Collinearity analysis further suggested that, throughout the evolutionary history of genus Oryza, the OSC genes have not undergone significant rearrangements or losses.Further functional analysis of 5 uncharacterized OSCs revealed that OsOSC10 was a friedelin synthase, which affected the development of rice grains. Additionally, the reconstructed ancestral sequences of Oryza OSC3 and Oryza OSC9 had lupeol synthase and poaceatapetol synthase activity, respectively.The discovery of friedelin synthase in rice unlocks a new catalytic path and biological function of OsOSC10. The pan‐genome analysis of OSCs within genus Oryza gives insights into the evolutionary trajectory and products diversity of Oryza OSCs. [ABSTRACT FROM AUTHOR]

Pre-clinical studies suggest that extracts prepared from the fruits of Vitex agnus castus (VAC) interact with dopamine D2 receptors, leading to reduced prolactin secretion. In previous experiments, dopaminergic activity was mostly evaluated using radioligand binding assays or via the inhibition of prolactin release from rat pituitary cells. Diterpenes featuring a clerodadienol scaffold were identified as major active compounds, but no conclusive data regarding their potency and intrinsic activity are available. Utilising advances in chromatography, we re-examined this topic using HPLC-based tracking of bioactivity via microfractionation of the VAC extract Ze 440. Using a cAMP-based assay, we measured dopaminergic activity in CHO-K1 cells that overexpress the human D2 receptor. Six diterpenes were isolated from two active HPLC microfractions. Viteagnusin I emerged as the most potent diterpene (EC50: 6.6 µM), followed by rotundifuran (EC50: 12.8 µM), whereas vitexilactone was inactive (EC50: >50 µM). Interestingly, triterpenes were also identified as active, with 3-epi-maslinic acid being the most active compound (EC50: 5.1 µM). To better understand these interactions at the molecular level, selected diterpenes and triterpenes were analysed through molecular docking against D2 receptor structures. Our data show that the dopaminergic activity of VAC diterpenes seems to depend on the configuration and on ring substitution in the side chain. This study also highlights for the first time the dopaminergic contribution of triterpenes such as 3-epi-maslinic acid. [ABSTRACT FROM AUTHOR]

Squalene is a natural triterpenoid and a biosynthetic precursor of steroids and hopanoids in microorganisms, plants, humans, and other animals. Squalene has exceptional properties, such as its antioxidant activity, a high penetrability of the skin, and the ability to trigger the immune system, promoting its application in the cosmetic, sustenance, and pharmaceutical industries. Because sharks are the primary source of squalene, there is a need to identify low‐cost, environment friendly, and sustainable alternatives for producing squalene commercially. This shift has prompted scientists to apply biotechnological advances to research microorganisms for synthesizing squalene. This review summarizes recent metabolic and bioprocess engineering strategies in various microorganisms for the biotechnological production of this valuable molecule. [ABSTRACT FROM AUTHOR]

A series of lupane‐type A‐ring azepanes modified at the C28, C30 positions and NH‐group have been synthesized and evaluated for cytotoxic activity against the NCI‐60 cancer cell line panel. Azepano‐betulinic amides showed pronounced activity, with a GI50 range from 0.57 μM to 14.30 μM, being 4–5 times more active than doxorubicin against colon cancer HCT‐15 and ovarian cancer NCI/ADR‐RES. It was established that azepano‐betulinic cyclohexyl‐amide acts preferentially through apoptosis induction both in conditionally normal and tumor cells, demonstrating mainly cytotoxic properties, whereas earlier studied azepano‐betulin acted by triggering the cell cycle arrest in cancerous cells and displayed mostly cytostatic activity. The crystal structure of N‐methyl‐azepano‐betulin hydrochloride salt was established by X‐ray diffraction method. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the stems of Bridelia stipularis led to the isolation of a new triterpene, 3β-O-trans-feruloylfriedelinol (1), together with five known compounds, friedelin (2), 3β-friedelinol (3), lupeol (4), stigmasterol (5), and 4-(1,5-dimethyl-3-oxo-4-hexenyl)benzoic acid (6). Their structures were identified by intensive spectroscopic analysis including 1D and 2D nuclear magnetic resonance, infrared, and mass spectrometry. Compound 1 showed significant α-glucosidase inhibitory activity (IC50 = 337.49 ± 0.59 µM) close to the standard, acarbose. Furthermore, the structure activity relationship of 1 was analyzed by molecular docking studies. In addition, the molecular docking results showed that the interaction between 1 and the active site occurred through hydrophobic forces and hydrogen bonds. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the leaves of Polyscias australiana (F.Muell.) Philipson (family Araliaceae) led to the isolation and identification of two new analogues belonging to the rare dammarane-type triterpene glycosides, polysciasosides B (1) and C (2). Also isolated in high yields from this plant was the known saponin, β-hedrin (3). The two new polysciasoside analogues exhibited no anti-inflammatory activity (inhibitory effects on NO inhibition and cell viability in RAW 264.7 macrophages) or cytotoxic activity against AGS gastric adenocarcinoma or the MCF7 breast adenocarcinoma cell lines. In contrast, the known compound β-hedrin exhibited potent anti-inflammatory and cytotoxicity in these biological assays. [ABSTRACT FROM AUTHOR]

The spirohydantoin-containing cucurbitane-type triterpenoid, kaguacidine A (1), was isolated and purified from 95% ethanol extract of vines of Momordica charantia L. (Cucurbitaceae). Its unprecedented chemical structure, a spirohydantoin substituent at C-23 of cucurbitane, was elucidated by extensive spectroscopic analyses, including HRESIMS, IR, optical rotation, 1 D- and 2 D-NMR spectra. The possible biosynthetic pathway is deduced and may be attributed to the metabolic activity of microbial symbionts in M. charantia L. Compound 1 was evaluated for anti-inflammatory activity against LPS-induced NO production in RAW 264.7 cells and anti-proliferative activity against four cancer cell lines, including HEp-2, MCF-7, Hep-G2, and WiDr. Compound 1 showed moderate anti-inflammatory activity with an IC50 value of 18.5 ± 0.4 μg/mL and weak anti-proliferative activity against MCF-7, HEp-2, Hep-G2, and WiDr with IC50 values of >40, 33.8 ± 0.6, 31.0 ± 0.7, and 27.0 ± 0.7 μM, respectively. [ABSTRACT FROM AUTHOR]

Four new polyoxygenated cucurbitane triterpene glycosides named kedrojiftene A-D (4-7), were isolated via different chromatographic techniques along with three phenolic compounds (1-3) from the crude extract of Kedrostis gijef. The isolated compounds were elucidated based on 1D, 2D-NMR spectroscopic analyses, HRESIMS and comparison with the related metabolites in literature. In bioassay, the α-glucosidase inhibitory assay for the isolated compounds was carried out and compounds (1-3) showed significant inhibitory activities. [ABSTRACT FROM AUTHOR]

ABSTRACT Squalene is a natural triterpenoid and a biosynthetic precursor of steroids and hopanoids in microorganisms, plants, humans, and other animals. Squalene has exceptional properties, such as its antioxidant activity, a high penetrability of the skin, and the ability to trigger the immune system, promoting its application in the cosmetic, sustenance, and pharmaceutical industries. Because sharks are the primary source of squalene, there is a need to identify low‐cost, environment friendly, and sustainable alternatives for producing squalene commercially. This shift has prompted scientists to apply biotechnological advances to research microorganisms for synthesizing squalene. This review summarizes recent metabolic and bioprocess engineering strategies in various microorganisms for the biotechnological production of this valuable molecule.

A new 2-quinolone alkaloid, iso-oligophyline (1), and two very unusual C34 terpenoids, proposed names ravespanol (2) and ravespanone (3), along with two known compounds, β-sitosterol (4), and methyl linoleate (5), were isolated from the leaf extract of Ravenia spectabilis engl. Methyl linoleate constitutes the first report of isolation from this species. We have already reported the isolation of atanine (6), oligophyline (7), ravenoline (8), and arborinine (9) from the plant. Based on nuclear magnetic resonance (NMR) spectroscopy and mass spectrometric analysis, the structure of the isolated chemicals was determined. The crude fractions and four compounds (6,7,8 and 9) were evaluated for a cytotoxicity study on a panel of six human stomach cancer cell lines (SCL, SCL-6, SCL-37′6, SCL-9, K-3, N21) by MTT assay. Among the plant extracts and isolated compounds, petroleum ether fraction and compound 7 exhibited the highest cytotoxic activity against SCL and SCL-6 cells, where the IC50 values were 17.9 and 16.56 μM, respectively.

Whitfordiodendron filipes var. tomentosum is an endemic plant in China. There have been no chemical or pharmacological studies of this plant reported before. In the current research, eight triterpenes and two steroids were obtained. Their structures were established by the analysis of NMR data and comparison with those reported in the literature. These ten structurally diverse compounds comprised five distinct carbon frameworks with different functionalities. The chemotaxonomic significance of these secondary metabolites was discussed, disclosing the common components between the variant W. filipes var. tomentosum and the species W. filipe. Evaluation of α-glucosidase inhibitory activities of these isolates disclosed that compounds 1, 2, 4, and 6 exhibited significant α-glucosidase inhibitory activities (IC50 = 16.6–19.2 μM), which were close in value to the positive control acarbose (IC50 = 11.5 μM). Moreover, the binding modes between the biologically active compounds 1, 2, 4, and 6 and the α-glucosidase protein were preliminarily studied using molecular docking. This study not only showed the chemical and biological profile of the plant W. filipes var. tomentosum but also revealed that these components could be developed as hypoglycemic lead compounds. [ABSTRACT FROM AUTHOR]

Background: Lung cancer is the predominant cause of cancer-related fatalities. This prompted our exploration into the anti-lung cancer efficacy of Labisia pumila, a species meticulously selected from the preliminary screening of 600 plants. Methods: Through the strategic implementation of activity-guided fractionation, ardisiacrispin A (1) was isolated utilizing sequential column chromatography. Structural characterization was achieved employing various spectroscopic methods, including nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR). Results: L. pumila 70% EtOH extract showed significant toxicity in A549 lung cancer cells, with an IC50 value of 57.04 ± 10.28 µg/mL, as well as decreased expression of oncogenes and induced apoptosis. Compound 1, ardisiacrispin A, induced a 50% cell death response in A549 cells at a concentration of 11.94 ± 1.14 µg/mL. Conclusions: The present study successfully investigated ardisiacrispin A extracted from L. pumila leaves, employing a comprehensive spectroscopic approach encompassing NMR, IR, and MS analyses. The anti-lung cancer efficacy of ardisiacrispin A and L. pumila extract was successfully demonstrated for the first time, to the best of our knowledge. [ABSTRACT FROM AUTHOR]

Background: Centella asiatica (CA) has been used to address cancer for centuries in traditional Chinese medicine (TCM). Previous studies demonstrated its anti-angiogenesis efficacy, but the underlying mechanism of its action remains to be further clarified. This study aims to investigate the underlying mechanisms of CA and its triterpenes in anti-angiogenesis for cancer therapeutics through network pharmacology and experimental validation. Methods: Cytoscape was used to construct a network of compound–disease targets and protein–protein interactions (PPIs) from which core targets were identified. GO and KEGG analyses were performed using Metascape, and the AutoDock-Vina program was used to realize molecular docking for further verification. Then, VEGF165 was employed to establish an induced angiogenesis model. The anti-angiogenic effects of CA were evaluated through assays measuring cell proliferation, migration, and tubular structure formation. Results: Twenty-five active ingredients in CA had potential targets for anti-angiogenesis including madecassoside, asiaticoside, madecassic acid, asiatic acid, and asiaticoside B. In total, 138 potential targets for CA were identified, with 19 core targets, including STAT3, SRC, MAPK1, and AKT1. A KEGG analysis showed that CA is implicated in cancer-related pathways, specifically PD-1 and AGE-RAGE. Molecular docking verified that the active components of CA have good binding energy with the first four important targets of angiogenesis. In experimental validation, the extracts and triterpenes of CA improved VEGF165-induced angiogenesis by reducing the proliferation, migration, and tube formation of human umbilical vein endothelial cells (HUVECs). Conclusions: Our results initially demonstrate the effective components and great anti-angiogenic activity of CA. Evidence of the satisfactory anti-angiogenic action of the extracts and triterpenes from CA was verified, suggesting CA's significant potential as a prospective agent for the therapy of cancer. [ABSTRACT FROM AUTHOR]

Introduction: Depending on their terpenoid and phenolic constituents plant resins can be classified as diterpenoid, triterpenoid or phenolic resins; thereby the profile of diterpenes and triterpenes is considered as genus‐ or even species‐specific. Objectives: We aimed to develop a simple, rapid, inexpensive, sensitive and specific method for the identification of resin‐specific triterpenoid and phenolic compounds in plant resins using (HP)TLC [(high‐performance) thin‐layer chromatography] combined with APCI‐MS (atmospheric pressure chemical ionisation mass spectrometry) and post‐chromatographic detection reactions. Methods: Twenty resin samples from different plant species were analysed. Different extraction procedures, post‐chromatographic detection reagents as well as various sorbents and solvents for planar chromatography were tested. To evaluate the potential of the optimised (HP)TLC‐APCI‐MS methods, parameter such as limit of detection (LOD) was determined for selected marker compounds. Results: Our protocol enabled qualitative analyses of chemotaxonomic molecular markers in natural resins such as dammar, mastic, olibanum and benzoin. For the first time, the application of thionyl chloride‐stannic chloride reagent for a specific post‐chromatographic detection of triterpenes is reported, sometimes even allowing discrimination between isomers based on their characteristic colour sequences. For triterpene acids, triterpene alcohols and phenolic compounds, detection limits of 2–20 ng/TLC zone and a system precision with a relative standard deviation (RSD) in the range of 3.9%–7.0% were achieved by (HP)TLC‐APCI‐MS. The applicability of the method for the analysis of resin‐based varnishes was successfully tested on a mastic‐based varnish. Thus, the method we propose is a helpful tool for the discrimination of resins and resin‐based varnishes with respect to their botanical origin. In this study, we developed a simple, rapid, cost‐effective, sensitive and specific method for the identification of chemotaxonomic molecular markers in plant resins such as dammar, mastic, olibanum and benzoin using (HP)TLC combined with APCI‐MS and post‐chromatographic detection reactions. For the first time, the application of thionyl chloride‐stannic chloride reagent for a specific post‐chromatographic detection of triterpenes is reported, sometimes even allowing discrimination between isomers based on their characteristic color sequences. [ABSTRACT FROM AUTHOR]

Coccinia grandis (C. grandis) is a perennial plant belonging to the Cucurbitaceae family. It is primarily native to Southeast Asia but has recently been cultivated domestically in Korea due to climate change. In this study, immature fruits of C. grandis, which are rich in bioactive substances, were processed into acidified pickles and stored for 15–55 days to investigate changes in their phytochemicals. The individual components of the phytochemicals in C. grandis were identified using an ultra-high-performance liquid chromatography system, and the main substances that were identified in this step then quantified using a triple quadrupole mass spectrometer. The qualitative analysis tentatively identified a total of 30 compounds (fourteen hydroxycinnamic acids, one hydroxybenzoic acids, thirteen flavonols and two triterpenes) in C. grandis pickles. Quantification of the phytochemicals showed that the major polyphenols—which included ferulic acid, p-coumaric acid, rutin and kaempferol—were highest on day 25 of aging and gradually decreased thereafter. Moreover, triterpenes decreased rapidly as the fruit was processed into pickles, and they further decreased with increasing time in aging. These results therefore indicate that C. grandis fruit has various bioactive substances that make it suitable for use in functional food development through pickle production.

Self-constructed water-in-oil emulsions can be stabilized by a natural pentacyclic triterpenoid, betulin. A higher betulin concentration (3%) results in smaller emulsion droplet sizes. Microscopy, confocal laser scanning microscopy and rheology indicate that the stabilizing mechanism is attributed to betulin crystals on the emulsion interface and within the continuous phase, thereby enabling excellent freeze/thaw and thermal stability. The betulin Pickering emulsion (1%) significantly increased betulin bioaccessibility (22.4%) compared to betulin alone (0.2%) and betulin-oil physical mixture (7.9%). A higher level of betulin at 3% leads to smaller emulsion particle size, potentially resulting in a greater surface area. This, in return, promotes a higher release of free fatty acids (FFA), contributing to the release and solubilization of betulin from emulsions. Additionally, it leads to the formation of micelles, further increasing betulin bioaccessibility (29.3%). This study demonstrates Pickering emulsions solely stabilized by phytochemical betulin provides an innovative way to improve its bioaccessibility.

Objective: Propolis of Tetragonula iridipennis, which is one of the most popular stingless bees found in Vietnam, has been used to promote health and prevent disease. This study aims to identify the chemical constituents of T iridipennis propolis and their cytotoxic activity. Methods: The propolis sample was extracted with ethanol. The crude extract was isolated by combined chromatographic methods. The structures of isolated compounds were determined by electrospray ionization mass spectrometry and nuclear magnetic resonance spectra. The cytotoxicity was evaluated by 3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide method. The protein interactions of active compounds were explored by molecular docking study. Results: Sixteen known compounds, including 11 triterpenes, 3 xanthones, a sterol, and a flavonoid were isolated and identified. The propolis ethanol extract displayed good cytotoxicity against A-549 and KB cancer cell lines. 24 S,25-Dihydroxytirucall-7-en-3-one was the most active compound with IC50 values ranging from 18.75 ± 0.21 to 19.62 ± 0.36 µg/mL. Conclusions: Sixteen known constituents were identified from T. iridipennis propolis, of which 8 compounds were discovered for the first time. The propolis of T iridipennis has multiple sources of plant resin, among that Ailanthus triphysa (Simaroubaceae) was identified as a new plant source. A molecular docking study revealed that cytotoxic effects of 24 S,25-dihydroxytirucall-7-en-3-one, α -mangostin, 6-methoxy–bispyrano xanthone, and 3-isomangostin related to the inhibition of all 3 targets epidermal growth factor receptor, human epidermal growth factor receptor 2, and mammalian target of rapamycin (mTOR), while other isolated triterpenes exert their cytotoxicity by the inhibition of mTOR protein activity. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the leaves of Camellia ptilosperma S. Y. Liang et Q. D. Chen led to the isolation of ten undescribed compounds, including six new triterpenes (1–6) and four new pheophorbide-related compounds (7–10). Meanwhile, the cytotoxic activity of the six triterpenes against six cancer cell lines was evaluated by MTT assay. Compound 2 showed potent cytotoxicity toward HepG2 cells with an IC50 value of 2.57 μM. Compounds 4 and 5 exhibited cytotoxicity against MDA-MB231 cells, with IC50 values of 11.31 and 5.52 μM, respectively. Additionally, the cytotoxicity of four new pheophorbides against these cancer cells was evaluated both in the presence and absence of light treatment. Compound 7 exhibited exceptional photocytotoxicity against Hela, MCF-7, and A549 cells, with IC50 values of 0.43 μM, 0.28 μM, and 0.92 μM, respectively. Compound 10 demonstrated significant photodynamic cytotoxic activity against BEL-7402 and HepG2 cells with IC50 values of 0.77 μM and 0.33 μM, respectively. The photodynamic antibacterial activity of 7–10 was also tested for S. aureus, E. coli, K. pneumoniae, and P. aeruginosa under direct illumination. Compounds 8 and 10 exhibited sensitivity to E. coli and demonstrated a photodynamic antibacterial effect, with a MIC value of 0.625 μM. [ABSTRACT FROM AUTHOR]

Centella asiatica is a medicinal plant with a rich tradition of use for its therapeutic properties. Among its bioactive compounds are centellosides, a group of triterpenoid secondary metabolites whose potent pharmacological activities have attracted significant attention. Metabolic engineering has emerged as a powerful biotechnological tool to enhance the production of target compounds. In this study, we explored the effects of overexpressing the squalene synthase (SQS) gene and transcription factor TSAR2 on various aspects of C. asiatica hairy root lines: the expression level of centelloside biosynthetic genes, morphological traits, as well as squalene, phytosterol, and centelloside content. Three distinct categories of transformed lines were obtained: LS, harboring At-SQS; LT, overexpressing TSAR2; and LST, simultaneously carrying both transgenes. These lines displayed noticeable alterations in morphological traits, including changes in branching rate and biomass production. Furthermore, we observed that the expression of T-DNA genes, particularly aux2 and rolC genes, significantly modulated the expression of pivotal genes involved in centelloside biosynthesis. Notably, the LS lines boasted an elevated centelloside content but concurrently displayed reduced phytosterol content, a finding that underscores the intriguing antagonistic relationship between phytosterol and triterpene pathways. Additionally, the inverse correlation between the centelloside content and morphological growth values observed in LS lines was countered by the action of TSAR2 in the LST and LT lines. This difference could be attributed to the simultaneous increase in the phytosterol content in the TSAR2-expressing lines, as these compounds are closely linked to root development. Overall, these discoveries offer valuable information for the biotechnological application of C. asiatica hairy roots and their potential to increase centelloside production. [ABSTRACT FROM AUTHOR]

Erigeron annuus L. is a flowering herb of North America, Europe, Asia and Russia. This plant is used as folk medicine in China for the cure of indigestion, enteritis, epidemic hepatitis, haematuria and diabetes. Phytochemical studies showed the presence of 170 bioactive compounds like coumarins, flavonoids, terpenoids, polyacetylenic compounds; γ-pyrone derivatives, sterols and various caffeoylquinic acids derived from the essential oil and organic extracts from its various parts such as aerial parts, roots, leaves, stems and flowers. The pharmacological studies demonstrated various extracts and the compounds of E. annuus to exhibit anti-fungal, anti-atherosclerosis, anti-inflammatory, antidiabetic, phytotoxic, cytoprotective, antiobesity and antioxidant activities. This article covers a critical compendious on geographical distribution, botanical description, phytochemistry, ethnomedicinal uses and pharmacological activities of E. annuus. However, further in-depth studies are needed to determine the medical uses of E. annuus and its chemical constituents, pharmacological activities and clinical applications. [ABSTRACT FROM AUTHOR]

In a previous study, we discovered that the ethanolic extract of sea buckthorn (Hippophae rhamnoides) fruits exhibited anti-osteoporosis effects both in vitro and in vivo. Through bioassay-guided fractionation, we identified the hexane fraction (HRH) as the active fraction, which was further fractionated using preparative HPLC. Among the resulting six fractions, HRHF4 showed significant activity. In the present study, we focused on the bioassay-guided isolation of bioactive compounds from the HRHF4 fraction. We successfully identified the active HRHF43 fraction, which led us to the isolation of potential bioactive compounds (1–6). The chemical structures of these compounds were determined using NMR data, LC-MS analysis, and HR-ESI-MS data as four triterpenes, ursolic acid (1), uvaol (2), oleanolic aldehyde (3), and ursolic aldehyde (4), together with two fatty acids, methyl linoleate (5) and ethyl oleate (6). To evaluate the efficacy of promoting osteoblast differentiation and the expression of mRNA biomarkers related to osteogenesis, we tested the isolated compounds in the mouse mesenchymal stem cell line, C3H10T1/2. Alkaline phosphate staining demonstrated that triterpenes (1–4) displayed osteogenic activity. Particularly noteworthy, ursolic aldehyde (4) exhibited the most potent effect, showing an 11.2-fold higher activity at a concentration of 10 μg/mL compared to the negative control. Moreover, ursolic aldehyde (4) upregulated the gene expression of bone formation-related biomarkers, including Runx2, Osterix, Alp, and Osteopontin. These findings suggest that the fruit extract of H. rhamnoides may have potential as a nutraceutical for promoting bone health, with ursolic aldehyde (4) identified as an active constituent. [ABSTRACT FROM AUTHOR]

Abstract The present work aimed to isolate secondary metabolites from Myrcia insularis Gardner (Myrtaceae) wood and to evaluate the anti-Candida activity and further extracts obtained by partition and the respective main isolated compounds. Wood was collected in a Seasonal Semideciduous Forest remnant of the Atlantic Forest of northern Rio de Janeiro State, Brazil. Chromatographic and spectrographic techniques were used to isolate and identify secondary metabolites. Methanol extract inhibited the growth of Candida buinensis and Candida tropicalis, with inhibition being approximately 82% for the latter. The main compound isolated from the ethyl acetate partitions was arjunolic acid, a triterpene. The antimicrobial activity was first observed with the wood metabolites of M. insularis adds to our understanding of the antifungal properties of this species and other species within the Myrtaceae family, including the presence of arjunolic acid, which may play a role in this activity.

A new lanostane-type triterpene, namely 3-oxo-5α-lanosta-7,9(11)-dien-24-oic acid methyl ester (2), and three known compounds including ganoderal A (1), ganoderiol B (3) and ganodermenonol (4) were isolated from the fruiting bodies of Ganoderma lucidum by silica gel column chromatography and Sephadex LH-20 column chromatography. Their structures were determined by extensive NMR data and mass spectral analysis. The in vitro cytotoxic activity of the isolated compounds against SK-Hep-1, HepG2, Hela and Hela/VCR cancer cell lines was assessed by using MTT assay. The IC50 values of compound 1 were 43.09 ± 2.86, 42.31 ± 1.78 and 46.51 ± 1.95 μM in SK-Hep-1, HepG2 and Hela cells, respectively, after 48 h. The IC50 values of compound 4 were 44.70 ± 2.32 and 41.33 ± 2.15 μM in Hela and Hela/VCR cells, respectively, after 48 h. [ABSTRACT FROM AUTHOR]

Introduction: Centella asiatica is an herbaceous plant reputed in Eastern medicine to improve memory. Preclinical studies have shown that C. asiatica aqueous extract (CAW) improves neuronal health, reduces oxidative stress, and positively impacts learning and cognition. This study aimed to develop and validate bioanalytical methods for detecting known bioactive compounds from C. asiatica in human biological matrices and apply them to a human pharmacokinetic trial in healthy older adults. Methods: High performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) was used for detecting triterpenes and caffeoylquinic acids from C. asiatica, or their metabolites, in human plasma and urine. Validation parameters including linearity, precision, accuracy, recovery and thermal stability were evaluated. The method was applied to a Phase I, randomized, double-blind, crossover trial of two doses (2 or 4 g) of a standardized C. asiatica water extract product (CAP) in eight healthy older adults. Pharmacokinetic parameters were measured over a 12-h post administration period and acute safety was assessed. Results: The method satisfied US Food & Drug Administration criteria for linearity and recovery of the analytes of interest in human plasma and urine. The method also satisfied criteria for precision and accuracy at medium and high concentrations. Single administration of 2 and 4 g of CAP was well tolerated and safe in healthy older adults. The parent triterpene glycosides, asiaticoside and madecassoside, were not detected in plasma and in minimal amounts in urinary excretion analyses, while the aglycones, asiatic acid and madecassic acid, showed readily detectable pharmacokinetic profiles. Similarly, the di-caffeoylquinic acidsand mono-caffeoylquinic acids were detected in low quantities, while their putative metabolites showed readily detectable pharmacokinetic profiles and urinary excretion. Discussion: This method was able to identify and calculate the concentration of triterpenes and caffeoylquinic acids from C. asiatica, or their metabolites, in human plasma and urine. The oral absorption of these key compounds from CAP, and its acute safety in healthy older adults, support the use of this C. asiatica product in future clinical trials. [ABSTRACT FROM AUTHOR]

Saccharomyces cerevisiae is widely used for producing various triterpenes by exploiting its native mevalonate/ergosterol pathway. Yeasts that accumulate phospholipids can produce more triterpenes. Our recent study demonstrated that a high phospholipid-accumulating yeast phenotype, as in spt10Δ yeast, results in increased endoplasmic reticulum (ER) biogenesis, resulting in ER expansion. However, the spt10Δ strain also exhibits high reticulophagy. Dgk1 (diacylglycerol kinase) is an important enzyme in lipid metabolism, which synthesizes phosphatidic acid (PA) by phosphorylating diacylglycerol (DG). We demonstrate that spt10Δ yeast with increased Dgk1 activity offer two desired results, (i) a highly expanded ER, due to redirection of the lipid pathway away from triglycerides towards phospholipid synthesis, increasing ER biogenesis; and (ii) decreased reticulophagy, by increasing the PA pool that activates TOR complex-mediated autophagy suppression. It was speculated that more ER-bound pathway enzymes can fit in the expanded ER, and the mevalonate-ergosterol pathway, being ER bound, might have higher activity. This was demonstrated by the co-expression of Dgk1 and plant triterpene synthase in spt10Δ yeast, which shows a high accumulation of plant triterpene.

The leaves of Zizyphus spina-christi (L.) Willd contain several compounds exhibiting different pharmacologic activities. However, studies on the cytotoxic activity of these compounds are limited. We aimed to investigate and isolate cytotoxic compounds with selective antitumor effects from the leaves of Z. spina-christi using bioassay-guided fractionation of methanol extract. Powdered, dried leaves were subjected to methanol extraction and fractionated using n -hexane, chloroform, ethyl acetate, and n -butanol. Fractions with positive cytotoxicity against HeLa and THP-1 cell lines were further fractionated and eluted using various concentrations of organic solvents. Active compounds were isolated using different chromatographic methods and their chemical structures were determined using extensive spectroscopic methods, such as 1D NMR (1H NMR, 13C NMR, and DEPT), 2D NMR (COSY, HMBC, and HMQC), HRFAB-MS, and IR. Furthermore, the cytotoxic effects of the isolated compounds were evaluated against 62 tumor cell lines (including HeLa and THP-1) in addition to normal bone marrow cells. The chloroform and aqueous methanol fractions of the leaves showed cytotoxic activity. Two compounds were successfully isolated and named "sidrin" (13-β-hydroxy-lup-20(30)-ene-2,3-β-epoxy-28-carboxylate) and "sidroside" (3- O -β-D-glucopyranosyl-(1–3)-α-L-arabinopyranosyl-jujubogenin-20- O -α-L-rhamnopyranoside). Sidrin exhibited cytotoxic activity against the human leukemia (Hl-60, RPMI-8226), lung cancer (A549, EKVX), breast cancer (BT-549, MDA-MB-231/ATCC), colon cancer (KM12), melanoma (M14, SK-MEL-5), and central nervous system (CNS) cancer (SF-295) cell lines, and selectivity was observed against the Hl-60, EKVX, BT-549, KM12, and SF-295 cell lines. In addition, sidrin was more active than sidroside and doxorubicin against the Hl-60 and EKVX cell lines. In contrast, sidrin had a similar effect to doxorubicin against the BT-549 and renal cancer (UO-31) cell lines. Sidroside was more selective against the leukemia (CCRF-CEM, MOLT-4), lung cancer (HOP-92, NCI-H322M), breast cancer (MDA-MB-468), melanoma (LOX IMVI), CNS cancer (SNB-19), ovarian cancer (OVCAR-8), renal cancer (UO-31, RXF 393), and prostate cancer (PC-3) cell lines. Both compounds exhibited similar activity against the breast cancer (MDA-MB-231, T-47D), colon cancer (HCC-2998, HCT-116), ovarian cancer (OVCAR-3), renal cancer (UO-31, 786–0, and SN 12C) cell lines. Normal bone marrow cells were unaffected at the same concentrations of sidrin and sidroside applied to tumor cells. These results suggest tumor-selective cytotoxicity of sidrin and sidroside. [ABSTRACT FROM AUTHOR]

Commersonia bartramia (Sterculiaceae family) is a wooden tree, widely occurring in Australia, China and South East Asia. The MeOH extract of C. bartramia has been reported to show anticancer and antioxidant activities. Phytochemical investigation of C. bartramia stems led to the isolation of eight compounds. Their chemical structures were identified as helichrysoside-3'-methyl ether (1), tiliroside (2), pinoresinol (3), ursolic acid (4), quercetin (5), kaempferol (6), vanillic acid (7) and 4-hydroxybenzoic acid (8) using NMR and MS spectral analysis. This is the first study about the chemical composition of C. bartramia. Among the isolated compounds, quercetin (5) showed good DPPH's radical scavenging activity with IC50 values of 11.43 ± 0.95 μg/mL, whereas the MeOH extract, (+)-pinoresinol (3) and kaempferol (6) displayed moderate activity. Quercetin (5) also displayed moderate cytotoxicity with IC50 values of 43.64 ± 3.63 to 61.58 ± 5.54 μg/mL. The MeOH extract exhibited weak cytotoxicity against HepG2, MCF7 and A549 cell lines. [ABSTRACT FROM AUTHOR]

Summary: Membrane‐localized transporters constitute important components for specialized metabolism in plants. However, due to the vast array of specialized metabolites produced by plants, and the large families of transporter genes, knowledge about the intracellular and intercellular transport of plant metabolites is still in its infancy.Cucurbitacins are bitter and defensive triterpenoids produced mainly in the cucurbits. Using a comparative genomics and multi‐omics approach, a MATE gene (CsMATE1), physically clustered with cucurbitacin C (CuC) biosynthetic genes, was identified and functionally shown to sequester CuC in cucumber leaf mesophyll cells.Notably, the CuC transport process is strictly co‐regulated with CuC biosynthesis. CsMATE1 clustering with bitterness biosynthesis genes may provide benefits and a basis for this feedback regulation on CuC sequestration and biosynthesis.Identification of transport systems for plant‐specialized metabolites can accelerate the metabolic engineering of high‐value‐added compounds by simplifying their purification process. [ABSTRACT FROM AUTHOR]

Introduction: Pink pepper is a worldwide used spice that corresponds to the berries of two species, Schinus terebinthifolia Raddi or S. molle L. (Anacardiaceae). Toxic and allergic reactions by ingestion or contact with these plants were reported, and classical in vitro studies have highlighted the cytotoxic properties of apolar extracts from the fruits. Objectives: Perform a non-targeted screening of 11 pink pepper samples for the detection and identification of individual cytotoxic substances. Methods: After reversed-phase high-performance thin-layer chromatography (RP-HPTLC) separation of the extracts and multi-imaging (UV/Vis/FLD), cytotoxic compounds were detected by bioluminescence reduction from luciferase reporter cells (HEK 293 T-CMV-ELuc) applied directly on the adsorbent surface, followed by elution of detected cytotoxic substance into atmospheric-pressure chemical ionization high-resolution mass spectrometry (APCI-HRMS). Results: Separations for mid-polar and non-polar fruit extracts demonstrated the selectivity of the method to different substance classes. One cytotoxic substance zone was tentatively assigned as moronic acid, a pentacyclic triterpenoid acid. Conclusion: The developed non-targeted hyphenated RP-HPTLC–UV/Vis/FLD–bioluminescent cytotoxicity bioassay–FIA–APCI-HRMS method was successfully demonstrated for cytotoxicity screening (bioprofiling) and respective cytotoxin assignment. [ABSTRACT FROM AUTHOR]

Drug delivery systems are technologies that have been vastly studied and applied to enhance existing therapies. For example, they allow the use of new approaches to already established drugs to improve the application of compounds with biological interest, such as augmenting their bioavailability. Betulinic acid (BA) is a triterpene that possesses interesting biological properties but its low solubility and low bioavailability have limited its applications. This work shows the obtention of BA and its incorporation process into two types of mesoporous silica, SN1(spherical) and SN2 (rod-shaped). Characterization of these materials through infrared, thermal analysis, scanning electron microscopy, and specific surface areas confirmed the presence of this triterpene in this silica matrix. Characterization of the BA release profile demonstrated that the probable mechanism of SN1 nanoparticles is a zero-order release system, whereas SN2 nanoparticles presented a non-Fickian diffusion. These results show the potential use of these nanoparticles as another approach in drug delivery systems for these types of compounds. [ABSTRACT FROM AUTHOR]

One new hopane-type triterpene, indicuen (1), along with eight known compounds (2–9) were isolated from the n-hexane extract of the lichen Parmotrema indicum Hale. The chemical structures of isolated compounds were identified by interpretation of their spectroscopic data (1D, 2D NMR and HRESIMS) combined with DFT-NMR chemical shift calculations and subsequent assignment of DP4+ probabilities and by comparison with the literature. Indicuen represents for a rare hopane bearing a 1-carboxyethyl substituent at C-21 in lichens. Compounds 1–3 and 5–8 were evaluated for α-glucosidase inhibition and cytotoxicity against K562 and HepG2 cancer cell lines. Compounds 1, 5 and 7 exhibited moderate α-glucosidase inhibition with IC50 values of 201.1, 156.3 and 187.4 µM, respectively. Compound 1 also showed weak cytotoxicity toward K562 cell line while others showed no activity. [ABSTRACT FROM AUTHOR]

Background: This study describes the isolation of major chemical constituent from the bark of Uvaria rufa Blume, commonly known as "allagat or susong kalabaw", an indigenous Philippine medicinal plant that belongs to the family Annonaceae. It is a short climbing shrub that grows in low and medium-altitude forests in the country. Materials and Methods: The bark samples of U. rufa were air-dried for three months without exposure to sunlight. The samples were ground in a blender, then, soaked in CH2Cl2 and in ethanol for three days and then, filtered. The crude extract of U. rufa was chromatographed on a gravity column dry packed with silica gel and was fractionated by silica gel chromatography using increasing proportion of acetone in CH2Cl2 at 10% increment. The purified isolates were subjected to NMR for structure elucidation. Their structures were identified mainly by using ¹H-NMR and by comparing current NMR data with those reported in the literature. Results: The results showed that the air-dried bark dichloromethane extract of the plant afforded glutinol. Glutinol and ethanolic extract exhibited anti-mitotic activity (18.33 % and 18.93 %, respectively), comparable to methotrexate (19.07 %), a well-known anti-cancer drug and even more potent in which they surpassed by 0.74 % and 0.14 %. Conclusion: The dichloromethane extract of the bark of U. rufa afforded glutinol that can be one the main metabolites responsible for the anti-mitotic activity of the plant. It may also contained other substances that might have great potential as novel therapeutic agents for cancer. [ABSTRACT FROM AUTHOR]

Whitfordiodendron filipes var. tomentosum is an endemic plant in China. There have been no chemical or pharmacological studies of this plant reported before. In the current research, eight triterpenes and two steroids were obtained. Their structures were established by the analysis of NMR data and comparison with those reported in the literature. These ten structurally diverse compounds comprised five distinct carbon frameworks with different functionalities. The chemotaxonomic significance of these secondary metabolites was discussed, disclosing the common components between the variant W. filipes var. tomentosum and the species W. filipe. Evaluation of α-glucosidase inhibitory activities of these isolates disclosed that compounds 1, 2, 4, and 6 exhibited significant α-glucosidase inhibitory activities (IC50 = 16.6–19.2 μM), which were close in value to the positive control acarbose (IC50 = 11.5 μM). Moreover, the binding modes between the biologically active compounds 1, 2, 4, and 6 and the α-glucosidase protein were preliminarily studied using molecular docking. This study not only showed the chemical and biological profile of the plant W. filipes var. tomentosum but also revealed that these components could be developed as hypoglycemic lead compounds.

Background: Lung cancer is the predominant cause of cancer-related fatalities. This prompted our exploration into the anti-lung cancer efficacy of Labisia pumila, a species meticulously selected from the preliminary screening of 600 plants. Methods: Through the strategic implementation of activity-guided fractionation, ardisiacrispin A (1) was isolated utilizing sequential column chromatography. Structural characterization was achieved employing various spectroscopic methods, including nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR). Results: L. pumila 70% EtOH extract showed significant toxicity in A549 lung cancer cells, with an IC50 value of 57.04 ± 10.28 µg/mL, as well as decreased expression of oncogenes and induced apoptosis. Compound 1, ardisiacrispin A, induced a 50% cell death response in A549 cells at a concentration of 11.94 ± 1.14 µg/mL. Conclusions: The present study successfully investigated ardisiacrispin A extracted from L. pumila leaves, employing a comprehensive spectroscopic approach encompassing NMR, IR, and MS analyses. The anti-lung cancer efficacy of ardisiacrispin A and L. pumila extract was successfully demonstrated for the first time, to the best of our knowledge.

Background: Centella asiatica (CA) has been used to address cancer for centuries in traditional Chinese medicine (TCM). Previous studies demonstrated its anti-angiogenesis efficacy, but the underlying mechanism of its action remains to be further clarified. This study aims to investigate the underlying mechanisms of CA and its triterpenes in anti-angiogenesis for cancer therapeutics through network pharmacology and experimental validation. Methods: Cytoscape was used to construct a network of compound–disease targets and protein–protein interactions (PPIs) from which core targets were identified. GO and KEGG analyses were performed using Metascape, and the AutoDock-Vina program was used to realize molecular docking for further verification. Then, VEGF165 was employed to establish an induced angiogenesis model. The anti-angiogenic effects of CA were evaluated through assays measuring cell proliferation, migration, and tubular structure formation. Results: Twenty-five active ingredients in CA had potential targets for anti-angiogenesis including madecassoside, asiaticoside, madecassic acid, asiatic acid, and asiaticoside B. In total, 138 potential targets for CA were identified, with 19 core targets, including STAT3, SRC, MAPK1, and AKT1. A KEGG analysis showed that CA is implicated in cancer-related pathways, specifically PD-1 and AGE-RAGE. Molecular docking verified that the active components of CA have good binding energy with the first four important targets of angiogenesis. In experimental validation, the extracts and triterpenes of CA improved VEGF165-induced angiogenesis by reducing the proliferation, migration, and tube formation of human umbilical vein endothelial cells (HUVECs). Conclusions: Our results initially demonstrate the effective components and great anti-angiogenic activity of CA. Evidence of the satisfactory anti-angiogenic action of the extracts and triterpenes from CA was verified, suggesting CA’s significant potential as a prospective agent for the therapy of cancer.

The cytochrome P450 monooxygenase (CYP) superfamily comprises hemethiolate enzymes that perform remarkable regio- and stereospecific oxidative chemistry. As such, CYPs are key agents for the structural and functional tailoring of triterpenoids, one of the largest classes of plant natural products with widespread applications in pharmaceuticals, food, cosmetics, and agricultural industries. In this review, we provide a full overview of 149 functionally characterised CYPs involved in the biosynthesis of triterpenoids and steroids in primary as well as in specialised metabolism. We describe the phylogenetic distribution of triterpenoid- and steroid-modifying CYPs across the plant CYPome, present a structure-based summary of their reactions, and highlight recent examples of particular interest to the field. Our review therefore provides a comprehensive up-to-date picture of CYPs involved in the biosynthesis of triterpenoids and steroids in plants as a starting point for future research.

Codonopsis lanceolata (Campanulaceae) is a perennial plant commonly known as the bonnet bellflower. This species is widely used in traditional medicine and is considered to have multiple medicinal properties. In this study, we found that shoots and roots of C. lanceolata contained various types of free triterpenes (taraxerol, β-amyrin, α-amyrin, and friedelin) and triterpene acetates (taraxerol acetate, β-amyrin acetate, and α-amyrin acetate). The content of triterpenes and triterpene acetates by GC analysis was higher in the shoot than in the roots. To investigate the transcriptional activity of genes involved in triterpenes and triterpene acetate biosynthesis, we performed de novo transcriptome analysis of shoots and roots of C. lanceolata by sequencing using the Illumina platform. A total of 39,523 representative transcripts were obtained. After functional annotation of the transcripts, the differential expression of genes involved in triterpene biosynthetic pathways was investigated. Generally, the transcriptional activity of unigenes in the upstream region (MVA and MEP pathway) of triterpene biosynthetic pathways was higher in shoots than in roots. Various triterpene synthases (2,3-oxidosqualene cyclase, OSC) participate to produce triterpene skeletons by the cyclization of 2,3-oxidosqualene. A total of fifteen contigs were obtained in annotated OSCs in the representative transcripts. Functional characterization of four OSC sequences by heterologous expression in yeast revealed that ClOSC1 was determined as taraxerol synthase, and ClOSC2 was a mixed-amyrin synthase producing α-amyrin and β-amyrin. Five putative contigs of triterpene acetyltransferases showed high homology to the lettuce triterpene acetyltransferases. Conclusively, this study provides the basis of molecular information, particularly for the biosynthesis of triterpenes and triterpene acetates in C. lanceolata. [ABSTRACT FROM AUTHOR]

Pentacyclic triterpenes, including lupeol, α- amyrin, and β-amyrin, present a large range of biological activities including anti-inflammatory, anti-cancer, and gastroprotective properties. The phytochemistry of dandelion (Taraxacum officinale) tissues has been widely described. Plant biotechnology offers an alternative for secondary metabolite production and several active plant ingredients are already synthesized through in vitro cultures. This study aimed to establish a suitable protocol for cell growth and to determine the accumulation of α-amyrin and lupeol in cell suspension cultures of T. officinale under different culture conditions. To this end, inoculum density (0.2% to 8% (w/v)), inoculum age (2- to 10-week-old), and carbon source concentration (1%, 2.3%, 3.2%, and 5.5% (w/v)) were investigated. Hypocotyl explants of T. officinale were used for callus induction. Age, size, and sucrose concentrations were statistically significant in cell growth (fresh and dry weight), cell quality (aggregation, differentiation, viability), and triterpenes yield. The best conditions for establishing a suspension culture were achieved by using a 6-week-old callus at 4% (w/v) and 1% (w/v) of sucrose concentration. Results indicate that 0.04 (±0.02) α-amyrin and 0.03 (±0.01) mg/g lupeol can be obtained in suspension culture under these starting conditions at the 8th week of culture. The results of the present study provide a backdrop for future studies in which an elicitor could be incorporated to increase the large-scale production of α-amyrin and lupeol from T. officinale. [ABSTRACT FROM AUTHOR]

Pennywort (Centella asiatica) is a herbaceous vegetable that is usually served in the form of fresh-cut vegetables and consumed raw. Fresh-cut vegetables are in high demand as they offer convenience, have fresh-like quality and are potentially great for therapeutic applications. However, it could be the cause of foodborne outbreaks. Pulsed light is known as a decontamination method for minimally processed products. The aim of this study was to determine the influence of pulsed light in combination with acidic electrolysed water on the sensory, morphological changes and bioactive components in the leaves of pennywort during storage. A combination of soaking with acidic electrolysed water (AEW) at pH 2.5 and pulsed light (PL) treatment (1.5 J/cm2) was tested on the leaves of pennywort. After treatment, these leaves were refrigerated (4 ± 1 °C) for two weeks and evaluated on the basis of sensory acceptance, the visual appearance of the epidermal cell and bioactive compounds. In terms of sensorial properties, samples treated with the combined treatment were preferred over untreated samples. The combination of AEW and PL 1.5 J/cm2 was the most preferred in terms of purchasing and consumption criteria. Observations of the epidermal cells illustrated that PL treatment kept the cell structure intact. The bioactive phytocompounds found in the leaves of pennywort are mainly from the triterpene glycosides (asiaticoside, madecassoside, asiatic acid and madecassic acid) and are efficiently preserved by the combined treatment applied. In conclusion, the combination of acidic electrolysed water and pulsed light treatment is beneficial in retaining the sensory quality and bioactive compounds in the leaves of Pennywort during storage at 4 ± 1 °C. [ABSTRACT FROM AUTHOR]

Phytochemical investigations of leaves and twigs from Garcinia oligantha Merr. resulted in the isolation of five undescribed triterpene derivatives (1–5) and six known analogs (6–11). Their structures were determined based on extensive spectroscopic data and high-resolution mass spectra analyses. Compounds 1–11 were tested for their in vitro cytotoxicity against three human cancer cell lines (HeLa, HepG-2, and MCF-7). Compounds 1, 2, 8, and 11 exhibited broad and significant cytotoxicity against the tested cell lines with IC50 values ranging from 5.04 to 21.55 μM. Compounds 5 and 9 showed cytotoxicity against HeLa and MCF-7 with IC50 values ranging from 13.22 to 19.62 μM. The preliminary structure–activity relationship for the 11 isolated compounds is also discussed. [ABSTRACT FROM AUTHOR]

[Display omitted] Lupeol, a triterpene derived from various plants, has emerged as a potent dietary supplement with extensive therapeutic potential. This review offers a comprehensive examination of lupeol's applications across diverse health conditions. By meticulously analyzing current scientific literature, we have synthesized findings that underscore lupeol's impact on cancer, diabetes, gastrointestinal disorders, neurological diseases, dermatological conditions, nephrological issues, and cardiovascular health. The review delves into molecular studies that reveal lupeol's ability to modulate disease pathways and alleviate symptoms, positioning it as a promising therapeutic agent. Moreover, we discuss the potential role of lupeol in clinical practice and public health strategies, emphasizing its substantial benefits as a natural compound. This thorough analysis serves as a critical resource for researchers, providing insights into the multifaceted therapeutic properties of lupeol and its potential to significantly enhance health outcomes. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the leaves of Camellia ptilosperma S. Y. Liang et Q. D. Chen led to the isolation of ten undescribed compounds, including six new triterpenes (1–6) and four new pheophorbide-related compounds (7–10). Meanwhile, the cytotoxic activity of the six triterpenes against six cancer cell lines was evaluated by MTT assay. Compound 2 showed potent cytotoxicity toward HepG2 cells with an IC50 value of 2.57 μM. Compounds 4 and 5 exhibited cytotoxicity against MDA-MB231 cells, with IC50 values of 11.31 and 5.52 μM, respectively. Additionally, the cytotoxicity of four new pheophorbides against these cancer cells was evaluated both in the presence and absence of light treatment. Compound 7 exhibited exceptional photocytotoxicity against Hela, MCF-7, and A549 cells, with IC50 values of 0.43 μM, 0.28 μM, and 0.92 μM, respectively. Compound 10 demonstrated significant photodynamic cytotoxic activity against BEL-7402 and HepG2 cells with IC50 values of 0.77 μM and 0.33 μM, respectively. The photodynamic antibacterial activity of 7–10 was also tested for S. aureus, E. coli, K. pneumoniae, and P. aeruginosa under direct illumination. Compounds 8 and 10 exhibited sensitivity to E. coli and demonstrated a photodynamic antibacterial effect, with a MIC value of 0.625 μM.

Abstract We examined the chemical constitution of the red alga Laurencia saitoi Perestenko, collected from Katsuura, Boso Peninsula, Chiba Prefecture, Japan. This specimen produced a new polyhalogenated acetogenin, named katsuurallene (1), which structure was determined by the spectral methods, along with known diterpene, deoxyparguerol (2) and triterpene, thyrsiferol (3). In this paper we describe the structural elucidation of katsuurallene together with some biological activities.

Cancer cells' resistance to anticancer drugs represents a major clinical problem and the most important failure of treatment. Combination chemotherapy is more effective than monotherapy due to additive or synergistic effects. The aim of our research was to assess the effects of the combinations of apple extract's triterpenic compounds, individual triterpenic acids, and doxorubicin (DOX) on human colon adenocarcinoma (HT-29) and human glioblastoma (U-87) cell lines in 2D and 3D cultures. The effect of the combination of apple extracts, the triterpenic standards, and DOX against HT-29 and U-87 cell viability was tested by the MTT and spheroid growth assays. Cell line HT-29 was more sensitive to DOX when incubated with all tested apple extracts than DOX alone. Cell line HT-29 was the most strongly sensitive to DOX when it was treated with 5 µM oleanolic acid (change of EC50 = −64.6% ± 4.4%) and with 5 µM ursolic acid (change of EC50 = −61.9% ± 8.8%) in 2D culture. Meanwhile, cell line U-87 was the most strongly sensitive to DOX when treated with 2 µM betulinic acid (change of EC50 = −45.1% ± 4.5%) in 2D culture. The combination of apple extract (E3) and DOX reduced the viability of HT-29 spheroids the most (spheroid viability reduced from −19.9% to −10.9%, compared to spheroids treated with DOX alone). Our study in 2D and 3D cultures showed that combining apple extract's triterpenic complexes or individual triterpenic acids with DOX may sensitize chemotherapeutic drugs and increase the cytotoxicity effects in HT-29 and U-87 cell lines. [ABSTRACT FROM AUTHOR]

Triterpenes are naturally occurring derivatives biosynthesized following the isoprene rule of Ruzicka. The triterpenes have been reported to possess a wide range of therapeutic applications including anti-viral properties. In this review, the recent studies (2010–2020) concerning the anti-viral activities of triterpenes have been summarized. The structure activity relationship studies have been described as well as brief biosynthesis of these triterpenes is discussed. [ABSTRACT FROM AUTHOR]

The attraction to the Euphorbia genus, with its remarkable diversity in species, is due to its variety of chemical compositions. Euphorbia turcomanica is one of the species of the spurge family growing wildly in Iran. This research aims to investigate the presence of secondary metabolites, specially terpenoid compounds, in terms of structural determination. Samples of E. tucomanica were finely powdered and macerated with acetone/dichloromethane 2:1. Repeated column chromatography using silica gel, MPLC, and HPLC methods followed by the analysis of data obtained from spectroscopic means was carried out to purify and identify the terpenoid constituents. The chemical structures of nine known terpenoids were determined for the first time from E. turcomanica during this study. Loliolide (1), a monoterpene, and eight steroids and triterpenes, including simiarenol (2), isomultiflorenol (3), cycloart-25-ene-3β,24-diol (4), β-sitosterol (5), cycloart-23-ene-3β,25-diol (6), 3α, 11α-dihydroxyurs-12-ene (7), 3β, 24β, 25-trihydroxycycloartane (8), and 7α-hydroxystigmasterol (9) were isolated and identified. E. tucomanica, with a rich terpenoid profile, can be one of the valuable and economic sources providing compounds for drug development. [ABSTRACT FROM AUTHOR]

We examined the chemical constitution of the red alga Laurencia saitoi Perestenko, collected from Katsuura, Boso Peninsula, Chiba Prefecture, Japan. This specimen produced a new polyhalogenated acetogenin, named katsuurallene (1), which structure was determined by the spectral methods, along with known diterpene, deoxyparguerol (2) and triterpene, thyrsiferol (3). In this paper we describe the structural elucidation of katsuurallene together with some biological activities. [ABSTRACT FROM AUTHOR]

Schinus molle is a plant traditionally used in Mexico to treat gastric disorders. However, no scientific evidence has been reported on its gastroprotective effect. The aim of the current contribution was to conduct a bioassay-guided study on S. molle to evaluate its gastroprotective activity in a model of Wistar rats given ethanol orally to induce gastric lesions. The hexane and dichloromethane extracts from the tested plant showed over 99% gastroprotection at a dose of 100 mg/kg. From the hexane extract, two of the three fractions (F1 and F2) afforded over 99% gastroprotection. The F1 fraction was subjected to column chromatography, which revealed a white solid. Based on the ESI-MS analysis, the two main compounds in this solid were identified. The predominant compound was probably a triterpene. This mixture of compounds furnished about 67% gastroprotection at a dose of 100 mg/kg. Pretreatment with L-NAME, indomethacin, and NEM was carried out to explore the possible involvement of nitric oxide, prostaglandins, and/or sulfhydryl groups, respectively, in the gastroprotective activity of the white solid. We found evidence for the participation of all three factors. No antisecretory activity was detected (tested by pylorus ligation). In conclusion, evidence is herein provided for the first time of the gastroprotective effect of S. molle. [ABSTRACT FROM AUTHOR]

Euphorbia officinarum L. is a Moroccan endemic plant known as "Tikiout" and "Daghmus" that can also be found in Mauritania, Western Sahara, and Algeria. In the present review, "Euphorbia officinarum", "metabolites" "hemisynthesis" were the keywords used for the research in the Web search engine Google Scholar and in the database Web of Science. Triterpenes, phytosterols and ingol diterpenes were isolated and identified in the latex of Moroccan E. officinarum. More than sixty triterpenes were obtained by hemisynthesis from natural triterpenes. Some of these derivatives had insecticidal and antimicrobial activity (phytopathogenic bacteria). The total phenol content and the antioxidant and anti-α-glucosidase activities were dependent on the time and temperature of extractions and also on the plant solvent ratio. The antioxidant activity of monofloral honey of E. officinarum origin was attributed to the phenol fraction (this fraction, previously isolated from honey samples, had better activity than the entire honey). [ABSTRACT FROM AUTHOR]

Triterpene scaffolds are cyclized by differential functional genes of the oxidosqualene cyclase (OSC) gene family, which are widely present in plant species. Thirty‐nine OSCs were identified from the hexaploid bread wheat (Triticum aestivum L.) genome. The gene structure organization and the distribution of conserved motifs of OSCs gene family revealed that the TaOSC proteins are highly conserved. By phylogenetic analysis, all OSC proteins from wheat and other cereal crops were clustered into 11 subfamilies (I–XI). Based on the publicly available transcriptional profiling, the tissue‐specific expression patterns of TaOSC during several developmental stages revealed diverged expression patterns, indicating that the TaOSC family has undergone subfunctionalization. Furthermore, homeolog expression bias was commonly detected in the TaOSC subfamilies, such as the expression of Ta5A004900 and Ta5D011800 in the subfamily II were specifically expressed in the leaf sheath and flag leaf sheath. In addition, two genes were strongly induced by Pst, indicating that the two homolog genes are involved in the resistance to powdery mildew. Molecular evolution analysis indicated that the TaOSC family genes were undergone purifying selection. So, the powdery mildew response may be very conservative and important biological function of the Ta5A004900 and Ta5D011800 in wheat. In conclusion, these results can be used to explore the diversity of triterpenes and clarify the mechanism of triterpene cyclization, and also provide useful information for future studies on the function of the TaOSC gene family in bread wheat and other important crops. [ABSTRACT FROM AUTHOR]